The Right Moment
by Rae94
Summary: Hiccup can't seem to work up the courage to make a move. A little help from his favorite "wingman" this Snoggletog could be just what he needs to convince him to go for it. Oneshot.


A/N: This is my very first posted story, and I am happy to say that it was written as a Secret Odin gift through Berk's Grapevine, which I hope you will check out! This story was written for Izzy.

Disclaimer: I do not own How to Train Your Dragon, nor any of its characters, settings, or ideas. They are the property of Cressida Cowell and Dreamworks Animation.

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**The Right Moment**

Toothless believed in seizing the moment.

In the year since the dragon's first Snoggletog on Berk, many things had changed about Hiccup. He had grown several inches—a development so joyous that he had actually _whistled_ while sewing new leggings for himself. His foot had gone through a few incarnations, partially as a result of his aforementioned growth spurt, and partially because he had so many ideas for improvements. And his hair, Toothless noted, was no longer confined to the top of his head, but was growing in patches on his face and chest.

All these changes made Toothless proud. The dragon, after all, had risked his own life to save Hiccup's, and he was glad every time some new evidence of the boy's maturation manifested. Toothless could even deal with Hiccup's increasingly daring stunts, accepting them as a sign that his rider was grateful to be alive.

So why was it, Toothless wondered constantly, that a boy who found freefalling life-affirming couldn't work up the courage to kiss a girl?

It wasn't that there weren't plenty of opportunities. On the contrary, the two teenagers spent a great deal of time together, carrying out their daily routines in almost perfect tandem. They had a ritual of feigning surprise when they "happened to bump into each other" on their morning flights, after which they would race back to Meade Hall for breakfast. Then it was off to the Academy, side by side. They fed their dragons together before sharing lunch themselves in the somnolent noonday sun. After a brief respite, they would reluctantly part ways: Hiccup to the smithy and Astrid to her own chores at home. As soon as they were done, though, they would rush to meet in the cove where Astrid put Hiccup through his paces with conditioning and combat training (Toothless and Stormfly used this time to spar a bit themselves). Finally, Hiccup would walk Astrid to her house for dinner with their dragons in tow.

And thus would commence the most awkward exchange known to Vikingdom.

"So," Astrid would say.

"So," Hiccup would respond.

Silence.

This would be followed by several seconds of hemming and hawing on Hiccup's part, before he would finally bid her farewell with as much eloquence as he was possessed of and make a hasty retreat.

"Ummm…S-see you tomorrow."

Toothless may not have understood the appeal of kissing, but he understood its importance, and what was at stake if it didn't happen. Upon their return to the Haddock family lodge every evening, he had taken to making his displeasure known in his customary manner:

_SMACK!_

"Ow!"

The first few times Toothless had done it, Hiccup had been upset ("What the Hel was that for?!").

After a few days, he would only grumble ("Yeah, yeah, I know.").

But the night before Snoggletog, Hiccup only let out a sigh before grabbing half a loaf of bread and a chunk of cheese from the table and clambering up the steps to his loft, shutting the door behind him with a solid _thunk_.

Toothless was left there, feeling incredibly frustrated and deeply guilty.

When Stoick arrived home a few minutes later, the dragon clambered outside, past the flustered chief, and up to the shuttered skylight. He scratched and purled as sincerely as he could, begging entrance to the loft, and waited.

Within a few moments, Toothless's keen ears detected the fastening of buckles and the soft _click-thump _of footsteps, and the shutters opened to reveal his rider's sad green eyes. Hiccup let out a deep exhale and gestured Toothless inside.

"C'mon, then."

The dragon padded in, keeping his body low to the ground, and gently placed his head beneath Hiccup's hand, which thankfully began to scratch him.

"I know, bud. I'm sorry too."

Hiccup took his seat at his desk, where a small wooden box sat beside a length of red ribbon. Toothless sniffed curiously at the box, and Hiccup took the hint and opened it.

Inside was a simple, silver, cable-like chain with a single embellishment hanging from it: a small, bright blue scale.

Hiccup took it out and explained, "She can wear it on her wrist. Not everyday, I mean—I mean, I know she won't want to wear it when she's, y'know, training and fighting. It's for special occasions. I know, I know, she doesn't usually wear any jewelry, and she likes to keep her forearms wrapped, but, maybe…"

His expression dropped.

"Oh, gods, this is a terrible idea. She's going to hate it. I should have made her a knife, or a hatchet, or—"

Toothless interrupted him with a bark, and Hiccup took a deep breath.

"I know I should just come out and say it. And it's not that I don't…you know…because I do. I do…"

He hesitated. Toothless nudged his side with his nose. Hiccup sighed.

"I love Astrid."

At this, Toothless gave a satisfied tremolo. Now they were getting somewhere! But Hiccup only groaned and fell back onto his bed.

"Well, it's easier to say to you than to her!"

The young man unbuckled his leg once more and settled into the furs. Accepting the end of this conversation for the time being, the dragon followed suit and laid down on his own rug. He was drifting off, when he heard a sarcastic murmur from the bed.

"Maybe Odin will leave me some courage in my helmet tonight, eh?"

Toothless's eyes shot open.

_Well, there's an idea._

* * *

Hiccup had the distinct feeling that he was being watched. Chalking it up to a dream, he opened his eyes to rid himself of the sensation, only to find himself staring directly into two bright green orbs.

"GAH!"

He scrambled away—off the bed and onto the floor.

"Ow!" He started to lecture his dragon as he righted himself, using the bedpost for balance. "Toothless, what were you thinking? Surely you can wait another hour to go fly—"

Bringing himself to a somewhat-standing position, he saw that Toothless had his prosthetic foot in his mouth.

"What are you doing with that?" Hiccup hobbled closer, still gripping the footboard to steady himself. But as he approached, Toothless backed out of reach.

"C'mon, you stupid lizard, I need that if you want to go flying." Hiccup hopped toward him; Toothless backed away again.

"Seriously? You wanna play keep away? Now, of all times?" Hiccup made a mad, one-footed leap for the crutches he kept by the headboard for emergencies. Toothless just gave a coughing laugh. No sooner had Hiccup gotten himself situated on the crutches, than with a telltale wiggle of his backside, the dragon bounded out the skylight and onto the ground below.

Hiccup let out a stream of colorful curses as he slid down the stairs on his rear and met Toothless outside in the early dawn. There, the Night Fury finally seemed content to give up the game, and he dropped the somewhat damp prosthetic at Hiccup's feet. Panting, Hiccup leaned on Toothless's back to buckle the harness around his knee.

"Just for that, I am revoking your indoor-sleeping privilege tonight, you dumb—hey, what do you have there?"

Toothless had turned his head back toward Hiccup, revealing a wooden box clamped between his gums.

"Aw, _COME_ _ON_!" Hiccup exclaimed, and the chase was on once more.

Even on two feet, Hiccup was no match for Toothless's speed. The large black blur zigged and zagged around houses and through the square, past dozing dragons and the occasional snoozing sheep. Hiccup eventually gave up on shouting at Toothless in favor of letting the rest of the tribe sleep.

When Toothless finally stopped, Hiccup was tired and ticked off. After catching his breath for a few moments, he rounded on the dragon and began to tug at the box in his mouth.

"Give me that, you troll-brained son of a salamander! Is this funny to you?! You think this is just a game of tug-of-war?! That thing took me FOREVER to get right, and I will not have it ruined by some bat-winged, overgrown—!"

"Hiccup?" a tired-sounding voice piped up from behind him.

Hiccup froze, eyes wide.

"You are so dead," he muttered, glaring at the Nigh Fury before turning with as much coolness as he could muster to the bleary-eyed blonde on the doorstep before him.

"Heeeey, Astrid. And a very happy Snoggletog to you! How are you doing this fine morning?"

Okay, maybe he laid it on a bit thick.

"Ummm…fine? Although I was planning on sleeping in a bit," she said hoarsely, smoothing her tousled hair. "…And yourself?"

"Great, just great." He looked pointedly at Toothless. "I was planning on sleeping in a bit this morning too, but—"

He stopped as the dragon placed the box gently on the ground and nudged it closer with a huge, blocky forefoot.

"But what?" Astrid prompted through a yawn.

"But…" Hiccup's expression softened at her sleep-tinged question. "But I couldn't wait to give you your gift." Hiccup picked up the box, wiping off the worst of the dragon slobber before handing it to the drowsy young woman. In a rumpled tunic, barefoot and shivering in the cold, he noted that she did not look quite so fierce as she did during the day.

Astrid opened the box with a gasp.

"Hiccup, it's…it's beautiful." She took it out and fumbled at the clasp with tired, uncoordinated fingers.

"Here, let me," Hiccup offered, and she extended her wrist for his assistance. When he had hooked it successfully, she withdrew her hand and examined the bracelet closely.

"It fits great, too. How long did it take you?" she asked.

"A couple of months," he admitted with a shrug. Astrid turned to look up at him, and Hiccup wondered when he had gotten tall enough for her to need to look _up_. The words that came out of his mouth next surprised even him.

"But not as long as this."

He kissed her suddenly, and Astrid made a small, surprised noise in the back of her throat. Hiccup softened the contact at the sound, and after a few seconds, he drew back.

Slowly, Astrid opened her blue eyes to meet Hiccup's green ones. Her cheeks flushed pink and her mouth worked soundlessly for a few moments, before he spoke.

"I love you, Astrid."

Finally, she found enough of her voice to reply.

"I love you too, Hiccup."

"So."

"So."

Toothless rolled his eyes and let out a descending whine.

"I'll see you later then?" Hiccup asked.

"Yeah…yeah, definitely."

"Alright." He began to walk back towards his house, when she called out.

"Hiccup?"

He spun around so fast he almost fell. "Yeah?"

"Thanks. You know…for the gift."

"Yeah. You're welcome."

And with that, the shivering girl shut the door.

Hiccup didn't need to look at Toothless to know that his companion was smirking like never before.

"What, no 'I told you so'?"

The dragon whiffed a negative.

"Good." The pair continued on their way silently, but Hiccup couldn't keep a stern face for long. A warm smile was creeping across his face, and he didn't try to stop it.

An identical expression crossed over his friend's face as they neared home. His chest puffed out with a parent's pride. Sometimes, all a hatchling needed to learn to fly was a little push when he least expected it.

And this hatchling had not disappointed him at all.

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A/N: Thanks for reading! Please leave me a review, and favorite the story if you like it. I would love the feedback. Happy Snoggletog!


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